


First Time's The Charm

by thelonelywriter



Category: Supernatural
Genre: Anal Fingering, Anal Sex, Bottom Castiel, Hair-pulling, M/M, Oral Sex, Plot What Plot, Porn Without Plot, Rough Kissing, Rough Sex, Scratching, Shameless Smut, Smut, Top Dean
Language: English
Status: Completed
Published: 2015-09-10
Updated: 2015-09-10
Packaged: 2018-04-20 01:08:44
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,139
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4767872
Author URL: https://archiveofourown.org/users/thelonelywriter/pseuds/thelonelywriter
Summary: <blockquote class="userstuff">
              <p>"You're sure about this?" Dean asks almost hesitantly from where both him and Cas sit on the edge of their bed in the bunker. Castiel nods, then looks over at Dean with a small smile.</p><p>"And you are too?" he questions, and Dean nods back.</p><p>"If you wanna try bottoming then I am more than willing to try topping," Dean states with an air of certainty to his voice. Castiel smiles softly once again before he leans over, and kisses him chastely, pulling away to look him in the eye. Dean cups one side of Castiel's face in his hand, and scooches closer, bringing him in for another kiss, this one more purposeful.</p>
            </blockquote>





	First Time's The Charm

**Author's Note:**

> AGAIN I'm am so sorry for not posting, I've been having an awful time lately with writer's block, and I've been juggling a lot of things!! With my excuses being thrown to the wind, have this fic!! This fic is pretty vanilla (sorry guys) and it didn't quite turn out the way I wanted it to, but I wanted to write a fic where Cas loves bottoming the first time he does it, soo this kinda happened... Side note: I experimented with the tenses in this fic, since I usually write all my fics in past tense, I wrote this one in present, and it's my first time writing in present tense so spare me!!

"You're sure about this?" Dean asks almost hesitantly from where both him and Cas sit on the edge of their bed in the bunker. Castiel nods, then looks over at Dean with a small smile.

"And you are too?" he questions, and Dean nods back.

"If you wanna try bottoming then I am more than willing to try topping," Dean states with an air of certainty to his voice. Castiel smiles softly once again before he leans over, and kisses him chastely, pulling away to look him in the eye. Dean cups one side of Castiel's face in his hand, and scooches closer, bringing him in for another kiss, this one more purposeful.

The two are only in jeans and t-shirts as they move onto the bed, the kiss growing deeper as Castiel willingly parts his lips, and Dean's tongue slides in with finesse, but also a certain sort of hunger, an air of expertness, of knowing where Castiel liked what, of what curls and flicks of his tongue drove him wild.

But tonight, Dean doesn't want to make things quick and dirty, he just wants to go slow, to take his time. Castiel soon realizes by the caressing movements and gentle touches of his hand just what he was doing.

Castiel smiles into the kiss when Dean fluidly lays him down on his back, and Dean drapes himself over Castiel, but makes sure not to crowd him, only to comfort him. Dean cups the back of Castiel's neck, never breaking the kiss that's sweet like honey, that always tastes better than Dean could have imagined. Castiel pulls slightly away only to nip at Dean's lower lip before he's moving forward once again, diving in for another addictive kiss. 

Dean runs his fingers through Castiel's hair, something he knows Castiel likes, and Castiel lets out a little purr mixed with a soft moan as their lips move together still. Dean brackets one arm by Castiel's head, using the other to smooth down his side, then slide teasingly up Castiel's shirt, loving the feeling of warm skin against his hand, loving the way Cas shivers at the roughness of it. 

Smiling softly, Dean leans down, brushing his lips against the skin of Castiel's neck. Castiel sucks in a breath of air at the hot tingles that bristle throughout him. He offers up his neck to Dean, tilting his head back the slightest so that Dean can press soft kisses to there, kisses that turn into little love bites, and then proceed to be bruises, marks of possession placed sloppily on his skin.

Castiel, breathing heavy, eyes fluttered closed, looks perfect to Dean, who practically eats up the sight, but still wants more. Dean coaxes Cas out of his t-shirt, lets it slide past his head before he's met with an expanse of tanned skin, and a chest that's rising and falling a little quicker than usual.

Dean licks his lips at the sight, straddling Castiel as he grasps onto his sides. Castiel can feel the heat of Dean’s hands, warm and calloused against the smoothness of his skin, running gently up his sides as Dean leans forwards, and lets his hands rest on Castiel’s ribs.

Kisses beginning at Castiel’s Adam’s apple soon run down and down, dappling themselves over Castiel’s hot skin until Dean reaches his nipples, smirking a little before flicking his tongue over one, listening to Castiel’s gasp in response. He runs his tongue around it, uses his hand to give attention to the other one, pinching and pulling it all whilst sucking and nipping and biting until Castiel is tugging at Dean’s t-shirt, shaky moans escaping his lips.

Dean lets Castiel help him quickly out of his t-shirt, throwing it, forgotten, to the other side of the room. Immediately, Castiel pulls Dean back down into a heated kiss, and Dean lets out a little noise of surprise that easily turns into pleasure when he feels Castiel rock his hips upwards into his. Dean lets Castiel take control for a moment, relaxing in his arms, on top of him, letting Castiel kiss him hungrily as Dean makes a languid rhythm of rolling his hips downwards. There are four layers of fabric separating them, but Dean could feel that Castiel was growing only harder and harder, and Dean was too with each lazy yet hungered grind between them.

Dean soon let's Castiel flip them over slowly until Castiel was fumbling to straddle Dean, and Dean was chuckling a bit at the way Castiel moved a little awkwardly in the moment, and Castiel just gave him this smile, Dean whispering, “Dork,” before Castiel murmurs affectionately,

“Shut up,” surging forward to kiss Dean once again, this time Dean’s hands coming up to cup the sides of his face, stroking over his cheeks before he was running his fingers through Castiel’s hair, loving the way it stayed so messy and mussed after every run through of Dean’s fingers. Dean moves his hands down Castiel's back, over his skin, relishing in the smoothness of it. Castiel rocks his hips down in a steady rhythm, rutting up against Dean quicker, more hurried this time.

Dean’s hands move further and further down until they’re cupping Castiel’s ass, bringing him forward and grinding him closer. Castiel lets out a soft moan, falling away from the kiss to rest his head in the crook of Dean’s neck as their hips move still in synchrony. “I need you naked, like now,” Dean groans quietly as Castiel lays down a particularly harsh rock of his hips. Castiel nips at the sensitive areas on Dean’s neck with a little grin before he’s rolling off of Dean, hooking his thumbs in the edge of his jeans and boxers and yanking them down, kicking them aside as Dean rushes to do the same.

Cas rises up onto his knees, going to straddle Dean, but before he knows it, Dean is pulling him down on top of him, kissing him furiously as he moans softly, the feeling of Castiel’s hot skin against his own enough to drive him crazy. Castiel nips at Dean’s lower lip, eliciting a moan from him before he licks back over the spot that tastes faintly of iron.

The air begins to grow hot and thick as their cocks slot together, and each of their breaths hitch in arousal as their bodies move desperately. Their hips undulate, the sweaty slide of skin on skin a beautiful sensation that they’ve been craving for what has felt like forever. Dean’s hands find Castiel’s thighs and lock around them, loving the twitch of muscle, they way his body moves in tune with them, with his hips too.

Their breaths are coming faster now as flooding pleasure trickles through them. Dean’s eyes are fluttering closed as Castiel rocks downwards with purpose. Finally, the fumbling fingertips on skin and the fluttering of eyelids and the sticky, sweaty movements all become too much, and Dean is pulling away from a heated kiss to murmur in Castiel’s ear. “Please tell me I can have you now.” For a moment Cas is confused with all the lust clouding his brain, but then he remembers that he won’t be the one on top this time, and a thrill of excitement and nervousness runs through him as he nods shyly. 

The position shifts so that Dean is on top, draped over Castiel, and Castiel is laying underneath him, watching him as he moves down his body, kissing over some of the bruises he made earlier. He moves back up slowly, nipping at Castiel’s ear. “Tell me if you want to stop, and tell me if anything feels uncomfortable, okay?” Dean states, looking Castiel in the eye with kindness. Castiel smiles, leaning up to give Dean a chaste kiss before nodding.

“I trust you, Dean,” Castiel tells him gently, and Dean smiles softly back.

“I trust you too, Cas,” Dean replies, kissing Castiel once more before he quickly slips off the bed, and returns with a bottle of lube.

Dean coaxes Castiel’s legs open as he lay back, taking deep breath, letting Dean’s hands simply smooth over his thighs, his breath slowly coming down to breathe over the sensitive skin on his inner thighs. Soon enough small kisses and little nips were being planted all over, trailing up to Castiel’s cock where Dean kisses up the underside, smiling at the shudder that runs through Castiel in response. His tongue then slips out, sliding up from the base to the tip before Dean takes the head in his mouth. 

Castiel unconsciously spreads his legs a tad wider as Dean’s hands find their way to Castiel’s hips where his thumbs rub little circles over the juts of his hipbones. His mouth suckles hard, collecting the salty precome that’s leaking out as his tongue darts in the slit, gaining a louder moan from Castiel, whose hands have found Dean’s head, and are grasping as best he can onto Dean’s shorter hair.

Dean soon pulls off slowly with a wet ‘pop,’ and Castiel mewls in protest, but Dean hushes him, soothing a hand over his thigh before taking it away to pour a good amount of lube onto one finger. Castiel’s head peeks up, looking at Dean who is looking down at him. “It’s gonna be cold, and it’ll feel weird at first, but just relax, and tell me if you don’t like it, and then we can stop. Sound good?” Dean proposes, and Castiel smiles softly and nods. Dean kisses the inside of Castiel’s knee with a little smile. “Good.”

Dean presses a slow, tentative finger to Castiel’s rim, and Castiel takes in the sensation. Dean circles his finger slowly to warm up the lube and to relax Cas as his other hand slides up and down Castiel’s inner thigh. Slowly, Dean pushes his finger in, cataloging Castiel’s reaction carefully as it goes up to the first knuckle. “How’s it feel?” Dean asks cautiously. Castiel tilts his head a little, thinking for a minute before his answer comes out.

“It feels odd. But keep going,” he reassures Dean, who carefully pushes his finger in further until he’s pumping it in and out, and Castiel is simply laying there, eyes closed, breathing steady.

“Can I add another?” Dean questions once he’s given Castiel some extra time.

“Yes,” Castiel answers simply, and his tone is almost breathy, so Dean slicks up another finger and gently slides it in with the first one.

At first, Dean doesn’t search for Castiel’s prostate, he simply stretches him carefully, watching him still. Then, after a minute, he decides to see how, exactly, Castiel will react to Dean brushing that spot that always has Dean, himself, in burning pleasure. Dean doesn’t have to search for long before he finds it, and when he does, he knows. Castiel clamps down on his fingers, taking a sharp intake of breath. “Bad, good, tell me,” Dean says simply as Castiel relaxes again.

“Good, very good,” Castiel sighs, and Dean strokes over it once more, and Castiel lets out a little sigh that’s so pretty Dean wants to capture it and play it on repeat.

Dean keeps stroking over that bundle of nerves, then hooking his fingers around Castiel’s rim, and soon enough, Castiel is breathing heavy, clutching the sheets. “How are you doing?” Dean asks, and Castiel groans softly.

“I’m, ah, good, keep going, just keep going,” he tells Dean, who grins, and slides another finger in. 

Dean only has to wait another minute before Castiel is panting, squirming on his fingers. But he makes sure to take the extra time to stretch him before he pulls his fingers out. Castiel whines softly at the loss, watching Dean get up to grab a condom. "So you're doing okay so far?" Dean double checks, and receives an aggressive nod in return. "Good," Dean continues. "You ready?" he follows up, and Castiel smiles and nods, so Dean takes a deep breath before slipping on the condom and applying a fair amount of lube.

Without command Castiel raises his legs to his chest, and Dean schooches between them. "I'll go in slow, okay?" Dean says softly, and Castiel nods once again before Dean leans in to give him a kiss, then pulls away, positioning himself against Cas.

He does as he had said, and let's just the head of his cock breach Castiel before he slides in halfway, then looks down at Cas. "How's it feel?" he pants, and Castiel wriggles around a bit underneath him, taking in the feeling. 

"It's strange, feels kinda weird," he states simply, and Dean nods. He's about to ask if Cas wants him to pull out, but then Castiel speaks up. "Good weird. You can keep going," he tells Dean who more than eagerly pushes in slowly until he can't go any further.

Dean allows them a minute or so because Cas feels so fucking tight and hot around him and he needs a moment to take that in, and Cas likely needs a moment to get used to Dean's dick inside of him. Dean pants hotly, and Cas breathes heavily. Finally, when Cas can't take it anymore, he speaks up. "You can move, Dean," he tells Dean, who doesn't ask once, simply thrusts in nice and shallow. A few more thrusts and Castiel's expressions change from confusion, to wonderment, to pleasure.

Dean, meanwhile, is grasping onto Castiel's sides was pressing messy kisses to Castiel's neck, lost in the feeling of Castiel underneath him, Castiel who was gripping Dean's back tight, eyes shut, breathing open mouthed. “That, oh God, that feels so good,” Castiel breathes out, relaxing completely into the sensation of it, of Dean who was pressed, bare skin, against him, sweaty and hot and just perfect. 

Castiel runs his hands up from Dean’s back to his neck, smoothing then through his hair. Dean groans into Cas’ skin, and Castiel starts grinding his hips up into Dean’s and that gains an even louder groan from Dean, whose panting breathlessly, and Castiel can tell that he’s holding back just by the way his hips twitch forwards with every thrust. “Harder,” Castiel demands with a hitched breath. “Dean, please,” he follows up pleadingly. Dean groans, long and low as he lets his hips go the way they want, fast and hard, bringing the level of heat in the air up by ten levels as Castiel desperately clutches onto Dean, his fingers digging into his back, and his legs tugging him forward as best they can.

It isn’t soon before Cas is crying out, digging his nails into Dean as Dean hits that spot inside him that’s sending sparks of pleasure all throughout of him. “Dean, yes, yes, _yes, ah,_ oh God,” Castiel manages breathlessly, and Dean moans at the way Castiel is clinging to him like there’s no tomorrow, at the way that he can see mussed hair and pink cheeks when he pulls away slightly.

“Fuck, Cas, you look so beautiful like this,” Dean praises through gritted teeth as he goes only harder, loving the way that Castiel’s mouth hangs open just the slightest, the way he’s breathing little, ‘ah’s,’ and ‘oh’s,’ under his breath that make Dean near the edge of his orgasm only quicker than usual. 

Soon enough, Castiel nails are scraping their way down Dean’s back, leaving red lines behind. Dean doesn’t mind though, it makes him equal with all the red marks and bruises he’s sucked into Castiel’s perfect skin. And then Castiel is moaning again, begging and sounding like a fucking porn star, but not that Dean cares because though he can’t hear himself because of all the blood rushing through him, pumping past his ears, he thinks that he’s probably making some pretty obscene comments and using some choice words, and in the back of his mind he’s so damn thankful for the fact that Sam is out.

“Dean, please, oh, I need you, need you,” Castiel gasps out, and Dean buries his head in the crook of Castiel’s neck with a moan. 

“I got you, Cas, don’t worry,” Dean manages to soothe, and Castiel fucking whimpers, meeting his hips greedily with Dean’s. 

Dean smooths his hands over Castiel’s sweaty skin, keeping up the pace of his hips as he looks down at Cas, simply admiring him. Castiel’s hands begrudgingly leave Dean and instead go for the mattress where he clutches the sheets with white knuckles as his back arches to get a better angle that he gladly vocalizes with his mouth slack jawed. “Oh, oh, Dean, ah, just like that, oh my God, don’t stop!” Cas nearly yelps, and Dean lets the sound, the words fill his ears as he slams into Cas just like he had asked to so kindly.

Castiel can feel a bone deep pleasure run through him, one he had never felt before, one that is only fueled by the sight of Dean above him, looking like he’s having the fucking time of his life pounding away into Castiel with his lip between his teeth and hooded eyes filled to the brim with lust. Castiel throws his head back against the pillow, feeling his orgasm coming closer than it had in awhile. But with Dean hitting that sweet spot with every thrust, with him looking so fucking gorgeous, so pleased, all while arousal that pooled deep inside him begins to blossom slowly.

The same pleasure ran through Dean, who was taking in the newfound feeling of being on top instead of the other way around, and taking it in with great joy. His hands search every inch of Castiel’s body as Castiel whines beneath him. “Dean, please, I’m close,” he pants, and Dean leans forward, kissing him harshly. The kiss is breathless and sloppy, but it continues as Dean reaches a hand down in between them, and wraps it around Castiel’s cock. Castiel moans loudly into the kiss as he arches up into Dean’s touch, and Dean can feel himself getting closer and closer as Castiel pants and whimpers and makes all these sweet little sounds into the kiss. 

It’s only a handful of rough strokes later that Castiel is coming with a gasp, come spurting between the two as his eyes fly open to display blue eyes swallowed by lust, and he clenches around Dean whose erratic thrusts stutter as his orgasm hits him only seconds later, and a swell of pleasure explodes inside both of them.

The two collapse bonelessly after Dean pulls out, limbs tangled, come splattered around and on them. Castiel hums lazily, pulling Dean in for one last kiss before he lets him go, and Dean beams back at him. Both of them wordless, still, Castiel manages to find some words that Dean strongly agrees with. “I think that this should happen more often.”

**Author's Note:**

> So, it'd be a great help to know what you guys thought of it, this one was kinda plain so sorry for that, but it's all I got recently :/ (Psst, here's [my tumblr](http://ughcas.tumblr.com):3)


End file.
